Damascenone

beta-Damascenone

Names
IUPAC name (E)-1-(2,6,6-Trimethyl-1-cyclohexa-1,3-dienyl)but-2-en-1-one
Identifiers
CAS Number	23726-93-4 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:67251 N
ChemSpider	4517997 Y
ECHA InfoCard	100.041.662
PubChem	5366074
InChI InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+ Y Key: POIARNZEYGURDG-FNORWQNLSA-N Y InChI=1/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+ Key: POIARNZEYGURDG-FNORWQNLBV
SMILES O=C(\C1=C(\C=C/CC1(C)C)C)/C=C/C
Properties
Chemical formula	C13H18O
Molar mass	190.29 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Damascenones are a series of closely related chemical compounds that are components of a variety of essential oils. The damascenones belong to a family of chemicals known as rose ketones, which also includes damascones and ionones. beta-Damascenone is a major contributor to the aroma of roses, despite its very low concentration, and is an important fragrance chemical used in perfumery.

The damascenones are derived from the degradation of carotenoids.

In 2008, (E)-β-damascenone was identified as a primary odorant in Kentucky bourbon.

The biosynthesis for β-damascenone begins with farnesyl pyrophosphate (FPP) and isopentenyl pyrophosphate (IPP) reacting to produce geranylgeranyl pyrophosphate (GGPP) Figure 1.

Next two molecules of GGPP are condensed together to produce phytoene by removal of diphosphate and a proton shift catalyzed by the enzyme phytoene synthase (PSY). Phytoene then goes through a series of desaturation reactions using the enzyme phytoene desaturase (PDS) to produce phytofluene then ζ-carotene. Other enzymes have been found to catalyze this reaction including CrtI and CrtP. The next series of desaturation reactions is catalyzed by the enzyme ζ-carotene desaturase (ZDS) to produced neurosporene followed by lycopene. Other enzymes that are able to catalyze this reaction include CtrI and CrtQ. Next lycopene goes through two cyclization reactions with the use of the enzyme lycopene β-cyclase first producing γ-carotene followed by the second cyclization producing β-carotene as shown in Figure 2.